


Chosen Sin

by NaomiJameston



Category: Critical Role (Web Series)
Genre: Angst, Heartbreak, Masturbation, Multi, Shameless Smut, Threesome - F/M/M
Language: English
Status: Completed
Published: 2020-10-20
Updated: 2020-10-20
Packaged: 2021-03-09 02:00:21
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,819
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27116464
Author URL: https://archiveofourown.org/users/NaomiJameston/pseuds/NaomiJameston
Summary: Caleb is lonely and thinking of the two people he loves, when suddenly they're there to help him.
Relationships: Jester Lavorre/Essek Thelyss/Caleb Widogast
Comments: 4
Kudos: 45





	Chosen Sin

**Author's Note:**

> This is my first time dabbling in the Critical Role fandom. Any mistakes made are completely mine, and please let me know in the comments.

It felt wrong to think of her in times like this. When his hand slicked along his thick length and his other hand, slippery with oil, pressed against his prostate deliciously. As much as he loved the fantasy of having her writhe beneath him, her blue skin beaded with sweat like her Genasi father- as much as he loved the feel of her skin beneath his and the thought of pressing his lips to hers, of exploring and delving and feasting and loving-

It all fell apart. For although he could see exactly how he would lead her to the bed, how they would fall into it with a laugh, and how they would curl together and stare at her painted skyline in post-coital bliss… It all faded when he thought of actually consummating their relationship.

Because when he thought about thrusting deeply into the person he loved, he didn’t see her bright, innocent yellow eyes. He didn’t see her blue skin purpling as her blush rose. No, he saw a deeper purple under his hands, a different set of eyes fluttering closed. White hair flying as he shivered around Caleb’s cock.

Essek was beautiful, there was no question about that. No one was immune to the man’s arresting good looks, least of all Caleb. And Essek was all the more beautiful as he panted and gasped under Caleb’s ministrations, pale fingers tracing deftly along sensitive purple hips to bring goosebumps to the flesh. 

Caleb groaned as he tightened his hand, imagining it was Essek’s tight entrance. He wondered what the man knew of carnal delights. What he could teach Caleb and what Caleb could teach him. They would learn from each other- likes, dislikes, experience together those curious things they’d wondered but never done. Jester would certainly know some. The Ruby of the Sea- the best lay ever- was sure to have taught her daughter a few tricks. 

But no, Jester was an innocent. She would never-

“Oh, I wouldn’t say ‘never,’ Caleb,” she said behind him. Before he could react, she slid on the bed before him, pressing her bare skin against his chest, warming what his passion sweat had cooled. He flinched, tried to turn, but was caught against another’s chest behind him.

“No, no. There’s no need to run away,” Essek said and pressed a kiss to Caleb’s neck. He chuckled as Caleb sputtered.

“This… This is not real,” Caleb said, breaking off into a groan as Jester caught his nipple between her teeth in just the way he liked.

“True,” Essek said, caressing Caleb’s cheek. “You are still in your cold, lonely bed with your finger up your ass, but that doesn’t mean you can’t enjoy yourself.”

“Yes, Caleb,” Jester said around his nipple, her hand reaching down to clasp his cock with deceptive innocence. “You are far too worked up. Essek and I only want to help you feel good.”

“This is… a trick.” But Caleb’s voice lacked conviction as Essek ran a wicked tongue along his neck and curled his hand around Jester’s and Caleb’s. The three pumped together and Caleb nearly spilled then and there.

“This is pathetic, even for me,” Caleb managed to mutter. Jester giggled.

“We can leave if you would rather?” she said, her wicked grin making it clear that she wouldn’t be going anywhere. Caleb shook his head fiercely.

“I am a damned man regardless. But it would be nice to earn a sin by choice for once.”

“A wise man,” Essek murmured against his skin. Though he was slight and fairly built, he had power behind him as he shoved Caleb forward. The pale wizard fell, crashing into Jester as he went and leaving them both sprawling. Caleb tried to push himself up, but Jester wrapped her arms around him.

“Don’t leave me, Caleb,” she pouted. Essek pressed his cool, nude body against Caleb’s back, holding him down.

“He’s not going to, Jester,” he said, his voice warm with a wicked grin. “Where would he run?”

She giggled, pressing a soft kiss to Caleb’s cheek. “That’s true. You can’t escape us. We’d follow you.”

Caleb huffed out an exasperated laugh. “I was not going to run. I was simply making room.”

Jester blinked at him, her eyes wide and innocent. “For what?”

Caleb didn’t respond, instead sliding a hand between them. His fingers brushed against her core, her folds already slick and warm. She writhed under him, making the most adorable sounds of delight. He continued his light exploration as he caught her mouth in a kiss, seeking permission with his tongue and delving in deep when she opened them. His fingers matched his tongue as he finally slid into her, curling them until he found the tiny bundle of nerves.

“Caleb!” she shrieked, arching her back and breaking their kiss. He took advantage of her position to trail his mouth down her neck, landing greedily on her puckered nipples. He sucked deeply, as she had done for him earlier. She keened, throwing her head wildly as he worked her body. 

A hand wrapped around his cock and a warm voice chuckled in his ear.

“Did you forget me?” Essek asked, his voice deep with lust and amusement. Caleb, still busy with hands and mouth, pressed back against the taller man in silent appeal. Essek didn’t say anything, but his fingers trailed around Caleb’s hips. One firm hand pumped Caleb’s cock while the other rolled his balls and tickled the sensitive skin around them. Caleb moaned around a mouthful of Jester’s breast. She hummed in agreement, arching to encourage him to suck harder. 

“She is beautiful, isn’t she?” Essek murmured against his skin. He continued his slow pumping on Caleb’s member as his hot mouth nipped and sucked along Caleb’s back, leaving love bites and hickeys in its wake. “So perfect. So needy. Yours for the taking, you know. You want her.”

Caleb keened against Jester’s skin, unashamed at the noise and the deep need that resonated through him. His fingers picked up their pace, thrusting in and out, and his thumb circled her clit in tight, sharp circles. 

She whimpered, chest heaving as she panted, “I’m close, so close!” 

Caleb pulled his fingers out, ignoring her whines, and his wet fingers trailed down her stomach. He slid his hands under his hips and lifted her as he lowered his head. Finally he latched his mouth onto her clit. Her frustrated pout was immediately replaced with a deep groan as he flattened his tongue and swiped and lapped at her greedily. It was only a matter of moments until she shattered around him, her thighs clamping around his head and her hands grabbing his hair.

He let her slide back down to lay against the sheets limply, body lightly twitching, her eyes blurred and a drunk smile on her lips. Unwilling to be forgotten yet again, Essek tapped his chin forcing Caleb to look back at him and finally pressed their lips together. Their tongues dueled, met, parted and met again. Essek hummed into Caleb’s mouth, the vibration traveling directly to his cock in a firestreak of lust. Caleb clutched at Essek’s chest to stay upright and moaned into the kiss.

“Fuck, that’s hot,” Jester said below them. Her cheeks were flushed deep purple watching them and one hand played idly with her nipple. Her eyes were bright with pleasure and purpose. She smiled sweetly and reached out gentle fingers to stroke along Caleb’s length, making his eyes flutter closed. “Take care of him, Essek. I’ve got this half.”

Essek left a final kiss to the corner of Caleb’s mouth and slid behind the human while Jester settled herself more directly under him. She canted her hips up and slid him between her wet lips, taunting him and herself, not letting him enter. Caleb huffed a frustrated sigh that turned into a yelp when Essek bit him gently on the ass. The drow held his hips firm and nuzzled at the wizard’s sensitive opening. Essek’s hot tongue slipped in easily, his way still prepared from earlier. Caleb groaned and tried to push back but the firm grip Essek had on his hips meant he only succeeded in thrusting into Jester’s hand. He shuddered at the sensation.

Essek’s finger replaced his tongue and pressed against the tight ring of muscle, drawing a rising whine from Caleb’s throat. It thrust gently, easily, his passage slick from Essek’s efforts and Caleb’s earlier masturbation. A second finger joined the first, then a third. They brushed against his prostate and Caleb threw his head back to let loose a strangled scream. They thrust in and out in the same rhythm that Caleb had used on Jester, and it was just as effective. He shuddered, moaned, begged for release, and almost didn’t notice the smirk Essek and Jester shared. 

In a fluid movement- a dance between partners- Essek entered Caleb who fell forward with a cry and entered Jester. The three moaned together, their cries of fulfillment echoing through the room. Caleb’s concentration faltered- it was so good, too good; he was going to-

“Caleb!” Jester whined and wiggled under him. “Move!”

He thrust automatically, pulling himself nearly off Essek’s length, before Essek pushed back into him with a snap as he pulled out of Jester. The Common tongue flew from his mind as the pressure built in his core. Most of his Zemnian fled, too, leaving him only with curses and inarticulate moans.

“Fick, fick, scheisse,” he said in rhythm with Essek’s thrusts. Jester locked her thighs around him, her ankles landing somewhere around Essek. Essek pulled them both tight against him, his deep purple hands trailing up Jester’s light blue skin and leaning forward so that Caleb could move freely between them.

Back and forth, filling and being filled, feeling and wanting and receiving and loving and-

Jester clamped tight around him, screaming her release. Her tight walls shuddering around him sent him over the cliff with her. He threw his head back and shouted nonsense phrases in Zemnian as he came. Essek was much quieter, biting into Caleb’s shoulder and grunting softly as he finished.

They breathed softly together for a moment before Caleb leaned forward to rest his face against his pillow. He pulled his hand from behind him and wiped it with a nearby cloth, repeating the action with his other hand. Slowly, methodically, carefully not thinking. 

He let himself collapse onto his side and shove a pillow over his face to muffle the sobs that rose from his chest to echo in the empty room.

There was no one there to love him. No one to hear him cry. No one to hear him whisper brokenly, “Ich hasse mich.”

It was better that way, of course. No one deserved to be saddled with a broken wreck of a man like him.

But Gott it hurt sometimes.


End file.
